Cytisine

Modify Date: 2024-01-02 18:16:53

Cytisine structure	Common Name	Cytisine
	CAS Number	485-35-8	Molecular Weight	190.242
	Density	1.2±0.1 g/cm3	Boiling Point	413.0±34.0 °C at 760 mmHg
	Molecular Formula	C₁₁H₁₄N₂O	Melting Point	154-156ºC
	MSDS	Chinese USA	Flash Point	203.6±25.7 °C
	Symbol	GHS06	Signal Word	Danger

Use of Cytisine

Cytisine is an alkaloid that occurs naturally in several plant genera, such as Laburnum and Cytisus. Cytisine is a partial agonist of α4β2 nAChRs[1], and partial to full agonist at β4 containing receptors and α7 receptors[2]. has been used medically to help with smoking cessation[3].

Name	cytisine
Synonym	More Synonyms

Description	Cytisine is an alkaloid that occurs naturally in several plant genera, such as Laburnum and Cytisus. Cytisine is a partial agonist of α4β2 nAChRs[1], and partial to full agonist at β4 containing receptors and α7 receptors[2]. has been used medically to help with smoking cessation[3].
Related Catalog	Signaling Pathways >> Membrane Transporter/Ion Channel >> nAChR Signaling Pathways >> Neuronal Signaling >> nAChR Research Areas >> Metabolic Disease
Target	α4β2 nAChRs[1].
In Vitro	Cytisine (2.5, 5 and 10 mM) is capable of inducing apoptosis in HepG2 cells[4]. Treatment with Cytisine increases the percentage of cells in the sub-G1 phase (P<0.01). The preincubation of HepG2 cells with Cytisine (2.5, 5 and 10 mM) significantly increases the sub-G1 cell population[4].
In Vivo	Cytisine (5 mg/kg, i.p.) eat less and gain less weight than those that receive the vehicle[2]. Total pellet intake increases during Cytisine substitution relative to nicotine and animals self-administered Cytisine significantly less than nicotine[2].
References	[1]. Pabreza LA, et al. [3H]cytisine binding to nicotinic cholinergic receptors in brain. Mol Pharmacol. 1991 Jan;39(1):9-12. [2]. Grebenstein PE, et al. The effects of noncontingent and self-administered cytisine on body weight and meal patterns in male Sprague-Dawley rats. Pharmacol Biochem Behav. 2013 Sep;110:192-200. [3]. Walker N, et al. Cytisine versus nicotine for smoking cessation. N Engl J Med. 2014 Dec 18;371(25):2353-62. [4]. Yu L, et al. Cytisine induces endoplasmic reticulum stress caused by calcium overload in HepG2 cells. Oncol Rep. 2018 Mar;39(3):1475-1484.

Density	1.2±0.1 g/cm3
Boiling Point	413.0±34.0 °C at 760 mmHg
Melting Point	154-156ºC
Molecular Formula	C₁₁H₁₄N₂O
Molecular Weight	190.242
Flash Point	203.6±25.7 °C
Exact Mass	190.110611
PSA	34.03000
LogP	0.07
Vapour Pressure	0.0±1.0 mmHg at 25°C
Index of Refraction	1.623

Cytisine MSDS(Chinese)

CHEMICAL IDENTIFICATION

RTECS NUMBER :: HA4025000

CHEMICAL NAME :: Cytisine

CAS REGISTRY NUMBER :: 485-35-8

BEILSTEIN REFERENCE NO. :: 0083882

LAST UPDATED :: 199709

DATA ITEMS CITED :: 12

MOLECULAR FORMULA :: C11-H14-N2-O

MOLECULAR WEIGHT :: 190.27

WISWESSER LINE NOTATION :: T C666 A GVN LM&TTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 8750 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 4(1),34,1941

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 101 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - rigidity (including catalepsy)

REFERENCE :: BJPCBM British Journal of Pharmacology. (Macmillan Press Ltd., Houndmills, Basingstoke, Hants. RG21 2XS, UK) V.34- 1968- Volume(issue)/page/year: 35,161,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 8550 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: CTYAD8 Zhongcaoyao. Chinese Traditional and Herbal Medicine. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.11- 1980- Volume(issue)/page/year: 18,214,1987

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 11764 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 4(1),34,1941

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1730 ug/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Behavioral - rigidity (including catalepsy)

REFERENCE :: BJPCBM British Journal of Pharmacology. (Macmillan Press Ltd., Houndmills, Basingstoke, Hants. RG21 2XS, UK) V.34- 1968- Volume(issue)/page/year: 35,161,1969

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 16 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85IXA4 "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948 Volume(issue)/page/year: -,589,1948

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - cat

DOSE/DURATION :: 400 ug/kg

TOXIC EFFECTS :: Behavioral - muscle contraction or spasticity

REFERENCE :: ITOBAO Izvestiya Akademii Nauk Tadzhikskoi SSR, Otdelenie Biologicheskikh Nauk. Proceedings of the Academy of Sciences of the Tadzhik SSR, Department of Biological Sciences. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) No.1- 1962- Volume(issue)/page/year: (2),104,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 5 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 4(1),34,1941

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 40 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85IXA4 "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948 Volume(issue)/page/year: -,589,1948 *** REVIEWS *** TOXICOLOGY REVIEW CTOXAO Clinical Toxicology. (New York, NY) V.1-18, 1968-81. For publisher information, see JTCTDW. Volume(issue)/page/year: 12,1,1978 TOXICOLOGY REVIEW PISDDJ Pacific Information Service on Street Drugs. (J.K. Brown, School of Pharmacy, Univ. of the Pacific, Stockton, CA 95211) V.1- 1972(?)- Volume(issue)/page/year: 5(3-6),-,1977

Symbol	GHS06
Signal Word	Danger
Hazard Statements	H301-H315-H319-H335
Precautionary Statements	P305 + P351 + P338
Personal Protective Equipment	Eyeshields;Faceshields;Gloves;type P2 (EN 143) respirator cartridges
Hazard Codes	T:Toxic
Risk Phrases	R25;R36/37/38
Safety Phrases	S26-S28-S36/37-S45
RIDADR	UN 2811
WGK Germany	3
RTECS	HA4025000
Packaging Group	III
Hazard Class	6.1(b)
HS Code	2933990090

Precursor 9
CAS#:667940-15-0 (6R,7R,9R)-(-)-... CAS#:206761-38-8 (3S,5R)-3-aceto... CAS#:667940-16-1 (3S,5R,1'S)-(-)... CAS#:667940-11-6 (3S,5R,1'R)-(-)...
CAS#:667940-18-3 benzyl (3S,5R)-... CAS#:667940-10-5 (3S,5R,1'S)-(+)... CAS#:667940-08-1 (3S,5R,1'R)-(+)... CAS#:485-35-8 Cytisine
CAS#:667940-14-9 (6R,7R,9R)-(+)-...
DownStream 3
CAS#:29047-52-7 12-(3-Aminoprop... CAS#:485-35-8 Cytisine CAS#:486-86-2 N-methylcytisine

HS Code	2933990090
Summary	2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Differential expression of the beta4 neuronal nicotinic receptor subunit affects tolerance development and nicotinic binding sites following chronic nicotine treatment.

Pharmacol. Biochem. Behav. 130 , 1-8, (2015)

The role of neuronal nicotinic acetylcholine receptors (nAChR) containing the β4 subunit in tolerance development and nicotinic binding site levels following chronic nicotine treatment was investigate...

Pharmacokinetics of cytisine, an α4 β2 nicotinic receptor partial agonist, in healthy smokers following a single dose.

Drug Test. Anal. , doi:10.1002/dta.1707, (2014)

Cytisine, an α4 β2 nicotinic receptor partial agonist, is a plant alkaloid that is commercially extracted for use as a smoking cessation medication. Despite its long history of use, there is very litt...

Synthesis and pharmacological evaluation of novel 9- and 10-substituted cytisine derivatives. Nicotinic ligands of enhanced subtype selectivity.

J. Med. Chem. 49 , 2673-2676, (2006)

We report the synthesis and pharmacological properties of several cytisine derivatives. Among them, two 10-substituted derivatives showed much higher selectivities for the alpha4beta2 nAChR subtype in...

CYTISINE

(1R,9S)-7,11-Diazatricyclo[7.3.1.0]trideca-2,4-dien-6-one

Cytitone

(1R)-1,2,3,4,5,6-Hexahydro-1,5-methano-8H-pyrido-[1,2-a][1,5]diazocin-8-one

1,5-Methano-8H-pyrido(1,2-a)(1,5)diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R,5S)-

1,5-Methano-8H-pyrido[1,2-a][1,5]diazocin-8-one, 1,2,3,4,5,6-hexahydro-, (1R,5S)-

(1R,5S)-3,4,5,6-Tetrahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2H)-one

MFCD00136048

Sophorin

Sophorin (VAN)

Ulexin

Cytisine (-)

Tabex

Tsitafat；Lupinidine

EINECS 207-616-0

Baptitoxin

(1R,5S)-1,2,3,4,5,6-hexahydro-8H-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one

Tsitafat

(-)-Cytisine

Ulexine

Cytiton

Sophorine

Cytisin

Baptitoxine

Laburnin

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China
Product Name: Cytisine
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China
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China
Product Name: Cytisine
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China
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Henan Tianfu Chemical Co., Ltd.
China
Product Name: TIANFU-CHEM CYTISINE
Price: $Inquiry/1kg $Inquiry/25kg $Inquiry/1000kg $Inquiry/10ton
Purity: 99.0%
Delivery: Inquiry
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Price: ￥500/10 mM * 1 mL in DMSO

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Cytisine

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